Dropbox wants to be the cloud solution enterprises turn to for online file sharing, but there’s a problem. At many companies, workers are prohibited from accessing the service. “It’s blocked,” were the two words we heard most often this morning when we asked a few dozen people to enter the site from their offices.

This is both a problem and an opportunity for Drew Houston, co-founder and CEO of Dropbox. And if reports are correct, he has a big pile of cash to throw at it.

Solving a Problem

Last Friday the Wall Street Journal and re/code both claimed Houston’s firm had raised $250 million from Blackrock and other investors. Each news source independently speculated that much of the money was earmarked for growing its business in the lucrative enterprise space.

It’s worth mentioning that less than a week earlier Dropbox users (most of who use it for personal file storage) were unable to access their files for what some claim to be almost 48 hours.

And while being separated from your collaborative family grocery list or the vacation photos your clan keeps on the cloud may not be that big a deal, not being able to access the price lists, contracts or design documents you need to show a client at a given moment may be embarrassing, disruptive and even costly.

But not nearly as costly as having cloud-residing corporate documents jam-packed with customer information, trade secrets, or business strategies exposed by hackers. That could cost millions, billions, even take down a business. That’s a risk most companies won’t take on, even if everyone loves a service like Dropbox.

Plenty of Uses

Secure file storage, access, and sharing are hardly the only reasons online file sync and share solutions are becoming “must have’s” in the enterprise — they’re also used for collaboration, mobile content management, document management, workflow, data exchange and so on …

And in many industries this means that regulatory, compliance and other rules must also be adhered to.

Needless to say, “Dropbox for Business,” almost by definition, has to be very different than Dropbox for consumers. Houston and his team seem to have recognized this, it’s why they’ve spent the past year building a new product which offers a handful of the same features as industry leaders (as defined by Forrester) like Box, EMC Syncplicity and IBM.

How Good is it?

News reports seem to indicate that Houston’s happy with his Dropbox for Business play. He has apparently kept the interface that everyone loves and put enterprise must-have’s, like permissions and security controls, under the hood. What he needs to do next is to get it out into the world, to see if end-users can be as happy with it as their personal Dropbox accounts in situations that test its Enterprise worthiness.

That’s where Houston (no pun intended) could have a problem because Dropbox for Business isn’t free (though there is a 14-day free trial). Though some (we’d even say many) rogue employees are probably thrilled using the consumer version at work, it will be difficult for them to recognize the benefits of Dropbox for Business without getting their coworkers on board or their employers’ consent (after all, someone has to pay the bill for the latter.)

And there’s not just that. It’s yet to be seen if Houston’s new product is truly enterprise-grade. We asked Jeetu Patel, General Manager of the Syncplicity unit at EMC, what the term “enterprise-grade” implies:

Enterprise-grade file sync and share requires three things. First, a consumer-grade experience that offers breakthrough innovations specifically for the business user. Second, it requires automated policy controls, security integration, and administration features so IT can deploy at scale. And last but not least, in this era of privacy and compliance concerns, it requires a SaaS deployment model that offers policy-driven control over where files are stored — both on premise and off premise in a hybrid cloud -- without any impact on user experience."

Vendors like Box, IBM and others in the space, no doubt, have their own definitions and their offerings, it should follow, that correspond with those definitions.

Taking on the Big Boys

It’s also worth noting that both “Enterprise-grade” and “Document Management” are terms that are sometimes readily said by vendors, but that carry big weight and accountability behind them. And when you’re selling to a decision maker who cares about security, controls and compliance, having experience and training in those spaces may very well matter.

This where Box, EMC Syncplicity and IBM are going to have distinct advantages over Dropbox, at least at this point in time.

And, yes, we know, some of you will be surprised that we put Box in the enterprise-savvy category. After all, its founders have probably never worked in an Enterprise or even had full-time jobs before they started Box.

While we certainly would understand the logic behind such an argument, we also feel compelled to consider who the company’s founders surround themselves with: Whitney Bouck, the General Manager of Box Enterprise, has nearly two decades of document management experience in the Enterprise. She knows what customers want, what they need and what they will pay for.

Box Enterprise’s lead architect, Victor Spivak, was a Principal Architect at Documentum (including after it became EMC Documentum) for nearly two decades as well, he has proven experience in delivering enterprise grade document management products. Add to that, Box’s team of Salesforce ex-pats, they know how to sell Software as a Service to the Enterprise.

EMC Syncplicity, it almost goes without saying, embodies enterprise-grade. Look who owns it. The company has it right when it claims “Enterprise is in our DNA.” It’s also true that EMC IIG, the division which owns Syncplicity, sets the gold standard for content management. It’s hard to remember a time (if there ever was one) where industry analysts such as Gartner, Forrester and Ovum, didn’t position the company as a leader. It’s also worth noting that Enterprise decision makers will open doors for EMC salespeople, so while they still need to have a great service to offer, they won’t have to establish trust and compliance the way Dropbox and Box might.

And then there’s IBM which, as far as we can tell, is selling mostly to the mothership’s customers. Why not? There’s more than enough turf to cover.

So what does all of this mean for Dropbox for Business? Despite Dropbox’s popularity on the consumer-side, it suggests that the company may have a bit of an uphill climb if it wants to win the Enterprise. And, not only that, but a climb against some pretty impressive competitors.

While we don’t know what EMC Syncplicity’s and IBM’s online sync and share sales figures look like (the companies don’t split them out), Box seems that it has better momentum, overall, than Dropbox. It outranks Dropbox in the App store and for a few days last week, the Box ioS app was one of the 10 most popular in the world.

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